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Reversible Control of Crystalline Rotors by Squeezing Their Hydrogen Bond Cloud Across a Halogen Bond-Mediated Phase Transition

Reversible Control of Crystalline Rotors by Squeezing Their Hydrogen Bond Cloud Across a Halogen Bond-Mediated Phase Transition

Cyprien Lemouchi, Hiroshi M. Yamamoto, Reizo Kato, Sergey Simonov, Leokadiya Zorina,Antonio Rodríguez-Fortea, Enric Canadell, Pawel Wzietek, Konstantinos Iliopoulos, Denis Gindre, Michael Chrysos, and Patrick Batail*.      Cryst. Growth Des., 2014, 14 (7), pp 3375–3383

Towards the synthesis of Schiff base macrocycles under supercritical CO2 conditions

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572010

A. M. López-Periago, C. A. García-González and C. Domingo,

Chem. Commun.,  46, 4315 - 4317, (2010)  DOI: 10.1039/c0cc00077a

The synthesis of Schiff base macrocycles was achieved using supercritical CO2 as both solvent and acid catalyst.


Over the past few years, the investigation of the synthesis of chiral imine macrocycles has become of growing interest.1 These Schiff based symmetric macrocyclic compounds offer an enormous potential in host–guest chemistry and molecular recognition, besides their additional potential applications as ligands and organocatalysts in asymmetric synthesis.2–3 The preparation of large polyimine meta- and para-macrocycles, also called trianglimines, has been successfully achieved using a classic synthetic strategy based on a [3+3] cyclocondensation (Scheme 1),4–7 where 3 units of (1R,2R)-diaminocyclohexane (1a) react with 3 units of an aromatic dialdehyde, either 1,3- (2) or 1,4-diformylbenzene (3), in a standard 0.4 M concentration in dichloromethane (DCM), yielding species 4a or 5a, respectively.

 

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